The Sly Cooper series introduced us to quite a few colorful enemies during its tenure on the PS2. From pirate frogs to clockwork birds, if you can think of an unlikely combination of animal-criminal, you’ve probably seen it while playing one of the Sly Cooper games. With such a arrangement of baddies, you’re bound to have some standouts, characters so out there or cool that you can’t help but remember them.
5.) Ms. Ruby

One of the more unusual bosses in the series, Ms. Ruby was a nasty alligator with a nasty attitude and nasty powers to match. Ms. Ruby makes her mark on this list with the company she surrounds herself with as well as her unique boss fight. Ms. Ruby not only has an army of zombified rats and ghostly cats, not to mention a gigantic anaconda caged and ready to be set loose on her unsuspecting enemies, but rhythm as well. So confident is she in her rhythmic superiority that she challenges you to a game based around it rather than fight you outright. It’s this affinity for all things musical and supernatural that cements Ms. Ruby as our # 5.

4.) Dimitri

A smooth-talking fashionista turned scuba-diver, Dimitri the Iguana is perhaps the biggest oddball in the entire line up. An artist turned counterfeiter, Dimitir isn’t exactly the coldest, most calculating criminal on our list. You just can’t take him seriously, everything he says and does seems like it’s part of an inside joke that Sucker Punch is letting us in on. Finally, it’s Dimitri’s strange attempts at new-age slang and enduring obsession with fashion make him our pick for most comical villain (and eventually ally) in the franchise.

3.) Panda King

Panda King just started off as the typical Kung-Fu themed boss that you’d expect to see in a game that features China as a location, but with Sly 3: Honor Among Thieves we get the opportunity to learn so much more about him. We discover that he is actually not simply a cold-hearted evil panda and like Dimitri, is on a mission to redeem himself. He is no hero however; he is a man at war with himself, seeking to find a balance between his dark and good personas. We see this just before the final mission at General Tso’s fortress as he argues with his dark half about whether or not to kill Sly. As the most characterized of all the villains, and whose motivations are the most complex of all Sly’s allies, Panda King captures our number 3 spot.

2.) Constable Neyla

Neyla gets our number 2 spot because she’s the one we never saw coming. All throughout Sly 2: Band of Thieves, she was the one who was sympathetic to Sly’s goals. It should have seemed suspicious but her expressed desire to take down the criminals no matter what it took had us thinking that she simply saw the law in a less absolute light than say Carmelita Fox. She plays Sly (and the player) so well that we don’t realize she’s double-crossed us until just before she reveals her true intentions and becomes “Clock-la”, a diabolical machine powered solely by her hatred for everyone around her. The former Constable Neyla manipulated us perfectly, and all I have to say about it is “well played…well played indeed”.

1.) Clockwerk

How could Clockwerk not be our most memorable villain? Not only did he keep himself alive for centuries on nothing but his hate, but his influence endured long after we “destroyed” him in the first game. Seriously, Clockwerk was bad enough as just a robotic bird, but as the second game unfolds we learn that each component of his metal body was itself something to fear, the eyes especially. Beyond all that, it’s Clockwerk’s motivation that sets him up as our most memorable villain. Every other criminal in the franchise is working for either wealth or power, but not Clockwerk. His sole motivation is hatred for Sly and his family, to the point where it’s his only reason to exist. He has no aspirations for power or wealth or even notoriety (which incidentally is why he wanted the Coopers out the picture in the first place), all he wants is the utter extermination of the Cooper clan. This is why we remember Clockwerk, for his utterly cold, unyielding, and unrelenting pursuit of satisfying his hatred. He is the true villain of the Sly Cooper franchise, and thus is Sly’s greatest foe, and my most-memorable villain.

These are my picks but what are yours? Is there another boss you think is more deserving to be on the list? How would you rank the Sly Cooper villains in terms how fun the boss fights were?